Will the line be sufficiently strong? The sheave width is .440 so using a 3/8 line will be pushing it. Still, the last thing I want is the halyward to break while out at sea. Stretch is another concern.

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Telstar 28
New England

You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.

—Cpt. Mal Reynolds, Serenity (edited)

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100% with Sailingdog and St Anna. 3/8 halyard or sheets is the minimun size for any line you will be handling for a sail more than 75 sq. ft or fifty pounds lift if you want to keeps your hands! 1/2 is really even better, I splice 3/8 into 1/2 on my 4 oz 150 jib sheets forward of the turning blocks.
They do make sheeves that are groved for both wire and rope just remember to size to the larger size halyard if your use spliced line. This is a case of bigger is better.

Another option if you want 5/16, is to go with a spectra inner core, less stretch, stronger than sta set. Something like XLS Xtra from sampson would work. i will also admit, the cost will be higher too. BUT, OTHER options do exist if you like smaller lines vs bigger diam ones.

I did the same thing on Argyle. Same deal, PO used wire and I wanted line. I used Zephyrwerks for the replacement sheaves and am quite happy. They work great.

I also used XLS extra for my jib sheet. I liked the feel of it better and spectra is supposed to have less long term stretch. I intend on putting on a roller furler (one of these days) on the forestay so I wanted minimal long term stretch.

Use 3/8. Larger is much more than you need for a 28' boat. Sta-Set-X is a really stiff line and a real bear to splice an eye. I've used the line of our 28 and now on or 38'. I intend to replace it with Samson XLS or one of the dyneema lines. You won't be happy with Sta-Set-X for the above reasons and because it coils poorly IMO.

For a boat that size 5/16" should be gross overkill for strength. My T-900 halyards are rated for about 7K# break strength.
Heck, your standing rigging is very likely no stronger than that.
Only caveat is making sure that the mast head sheave will handle line (i.e. shape of groove and no scars/ridges in the metal to abrade the new line.
Also, be sure that your particular clutch stoppers will hold.

When replaced all out old halyard wires (meat hooks... yikes) in about '02, we found that 3/8 line was a bit too wide for the sheaves and that the 5/16 would hold in the old clutches. Got lucky. Our boat is 34' long, FWIW.

It's not only breaking strength, it's stretch. If going with a dacron double braid, I wouldn't go less than 3/8. You can easily get away with 5/16 if you go with a higher tech line. I replaced the wire/rope main halyard on my previous 30 footer with 5/16 Ultra-Tech. No problems with handling and line was holding up well after five years of use. Had the rigger put in an eye splice as that was beyond my skills for that kind of line.

Good idea on replacing sheaves. Stay away from Sta-Set X. The stuff is hard to splice, stiff, and doesn't run well. 5/16 (8MM) is fine for a boat your size but be sure that your rope clutches are sized for it. I have had great success with New England's VPC on my C&C 29-II which has very similar rig dimensions. My 120lb wife has no trouble at all raising the main or headsails with 5/16" VPC.

VPC has a polyester cover with a blended core of Vectran and another polyolefin. Lower stretch than Sta-Set X with a moderate price. Expect to find it online at $.85-$1.00/ft.

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